
Family-friendly vacation rentals in Jamaica
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Top-rated family-friendly rentals in Jamaica
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Popular amenities for Jamaica family-friendly rentals
Family-friendly home rentals with a hot tub

Top of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Secluded Farmhouse Retreat - stunning views
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.

Okemo Ski Chalet with Hot Tub
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

Peaceful cabin close to skiing & Brattleboro
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

Ski Chalet with Hot Tub on Okemo Mountain
Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!

Expansive Lakehouse with Jacuzzi
My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!

Spacious Renovated Barn Apt on 100 acres!
My wife and I have visited twice already and hope to go back again soon. We met the owner and her wonderful fiancé while we were visiting. Wonderful people. Very private and beautiful location. If you need to unwind and relax this is the location for you. Thank you for hosting us and congratulations..
Family- and pet-friendly home rentals

Walk to Village/Lake Whitingham
Great little studio apartment attached to Emily’s house, very peaceful yet walkable to downtown Wilmington!!! Easy to get to the Hoot and Toot trail, and about a mile from the boat launch/picnic grove at the lake!! Absolutely would recommend and stay again!!

Cottage
A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.

400+ Airbnb Visits: Incredible Mountain Cabin
We had a wonderful stay at Ali and Carson’s cabin! They were incredibly helpful and welcoming hosts. The Mountain View from the cabin is absolutely stunning, even with the rainy weather, it was breathtaking. We also enjoyed exploring the charming nearby towns, and our two dogs had a great time as well. Despite the rain, we loved our stay and are already looking forward to coming back when the weather is better. Highly recommend!

Pinecone Pond
We had the most lovely stay at Pincone Pond. The house is absolutely spotless and well stocked with everything you need in the kitchen, shampoo and condition in the bathrooms and throw blankets for the cool evenings. The house is so homey and comfortable and the grounds are stunning. Beautiful yard and pond which were well cared for. Catherine has thought of everything including chairs for sitting by the pond or fire pit. Just a lovely, peaceful spot.

The Carriage Barn
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER
Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!

Comfortable farmhouse with stunning views
This was the perfect place for a peaceful Vermont getaway! The house is unique and a great balance of historical farmhouse and modern comfort. Very clean and easy to use amenities. Would love to stay again!

Yurt In The Woods - Private Refuge
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!

Bear's Den - Mt Snow Townhome w/ Heated Pool!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Mt Snow Ski In/Out at Seasons
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

Moon Valley Country Retreat no clean fee pets yes
Great place to stay. Quiet and secluded. Has everything you need. Great host.

Cozy Bear- 1 mile to Mt Snow Ski Home
We really loved staying here. The location was perfect and the accommodations were fantastic. Our host was exceptional in making sure we were comfortable and informed. We will definitely try to book again.

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

Luxury King, fireplace, pvt entrance- Farmhouse 1
Wonderful stay at Farm Road Estate! Clean, private, with a peaceful vibe and gorgeous area. The room itself was amazing and spacious, and lighting the fireplace at night in our room was an added bonus. The bar/restaurant on the grounds wasn’t open when we stayed, so looking forward to staying here again when it is open! Definitely need a car to travel and explore the town/surrounding towns. There are some good restaurants and bars within a less than 10 minute drive! 5/5 stars!

Hollywood Bungalow in the Berkshires #C0191633410
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Quick stats about vacation rentals that are family-friendly in Jamaica
Total rentals
170 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
8.4K reviews
Pet-friendly rentals
80 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
160 properties include access to wifi
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Dorset Field Club
- Autumn Mountain Winery
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Ekwanok Country Club